Table 1.

Oxidative cleavage of aliphatic epoxides

Entry yieldb	Substrate	Product	Solvent	NaIO4a (equiv)
1			CH3CN/H2O	5	73%
2			CH3CN/H2O	5	58%c
3			CH3CN/H2O	4	78%
4			THF/H2O	2	67%
5			THF/H2O	2	91%
6			THF/H2O	2	88%
7		X = H	CH3CN/H2O	2	84%
8		X = p-Cl	CH3CN/H2O	2	34%
9		X = p-F	THF/H2O	2	62%
10		X = o-Br	CH3CN/H2O	2	71%d
11			CH3CN/H2O	2	41%e
12			CH3CN/H2O	2	64%

^aA significant drop in pH occurred with the addition of NaIO₄ to the THF/H₂O mixture (pH 6 to pH 4).

^bIsolated yield.

^cStarting material was recovered in 39% yield.

^dBased on recovered starting material.

^eOnly PhCHO was observed.